Description
Carpropamid is a rice fungicide. It is not very soluble in water, volatile and, based on its chemical properties, it is non-mobile. Little is known regarding its persistent in soil and aquatic systems. It is not highly toxic to mammals. It shows a moderate level of toxicity to birds, fish and earthworms.
Definition
ChEBI: A cyclopropylcarboxamide obtained by formal condensation of the carboxy group of 2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxylic acid with the amino group of 1-(4-chlorophenyl)ethylamine. A rice fungicide with specific action against Pyricularia
ryzae. It is not highly toxic to mammals but shows a moderate level of toxicity to birds, fish and earthworms.
Production Methods
Carpropamid is synthesised through a targeted condensation reaction that forms its distinctive cyclopropylcarboxamide structure. The production begins with 2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxylic acid, which is reacted with 1-(4-chlorophenyl)ethylamine. This formal condensation of the carboxylic acid group with the amine yields the active compound, carpropamid.
Mechanism of action
Systemic, protective, melanin inhibiting - no curative properties but does induce disease resistance in rice plants. Shown to be a potent inhibitor of scytalone dehydratase, the target enzyme in the melanin biosynthesis pathway of the rice blast fungus.
Metabolic pathway
Carpropamid is degraded gradually and in a similar
way in rice plants (including rice cell cultures),
mammals, typical paddy soils, and water. The
degradation process includes oxidation of the methyl
group of the cyclopropane ring or in the 4-chlorophenyl
ring. In mammals and plants, various water-soluble
conjugates are formed. In soils, carpropamid is
completely degraded to carbon dioxide.
